


City of Angels

by WingsandImpalas



Category: Supernatural
Genre: Alternate Universe - Pretty Woman Fusion, Angst and Fluff and Smut, Bisexual Dean Winchester, Bottom Castiel/Top Dean Winchester, CEO Dean Winchester, Closeted Dean Winchester, D/s undertones, Endverse Cas/Dean Smith, Eventual Happy Ending, Eventual Romance, From Sex to Love, M/M, Military Veteran Castiel (Supernatural), Miscommunication, Mutual Pining, POV Alternating, Pansexual Castiel (Supernatural), Past Castiel and others, Past Dean and others, Plot With Porn, Prostitute Castiel (Supernatural), Prostitution, Recreational Drug Use, Semi-Public Sex, Top Castiel/Bottom Dean Winchester, Touch-Starved Dean Winchester
Language: English
Status: In-Progress
Published: 2020-06-10
Updated: 2020-06-24
Packaged: 2021-03-04 04:14:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 11,432
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24647785
Author URL: https://archiveofourown.org/users/WingsandImpalas/pseuds/WingsandImpalas
Summary: Dean Smith never takes take’s a risk. He never gambles, never lets his heart get in the way of his head. Sure, he’s business savvy, but he never tries to make a deal he knows he can’t win. So, of course, its while he’s stuck in the city of angels trying to close the biggest deal of his career he meets Castiel.A blue-eyed, leather-wearing, Prostitute who makes Dean want to live life on the edge.Ironically, when it comes to Castiel’s job, there’s a lot of rules. They’ve helped keep him safe over these past few years working his corner. But the big one has always been never let it be personal. Never kiss on the mouth, never let it get too intimate and never ever fall in love with a John.So, of course, it would be Dean Smith, a strait-laced, rule-abiding, stick in the mud that makes him question that very rule.
Relationships: Castiel/Dean Winchester, Endverse Castiel/Dean Smith (Supernatural)
Comments: 9
Kudos: 41





	1. Chapter 1

**Author's Note:**

> AHHHH It's here!!!!
> 
> This fic is my purely self-indulgent birthday fic as a gift to myself because God do I love this movie. I've messed around with the time zone a bit, setting it in 2009 instead of the 80s because I'd get too into the research. As you can see in the tags this is an Endverse Cas/Dean Smith fic because I love that pairing and I thought it would be really fun to do with this movie. However because of those characterisations its definitely going to change their pretty woman counterparts personalities. Because I refuse to believe Dean Smith is as cool as Edward. 
> 
> As with all of my fics I have a [Pinterest board](https://www.pinterest.co.uk/wingsandimpalas/city-of-angels/) made up if you want to get the vibe I am setting for this fic and a [playlist made](https://open.spotify.com/playlist/6dEPwrIN1Z66uizjHDYn9R?si=QhKlwriIT9uy5cTveDvMZg).
> 
> All in all this fic is a good bit of cheesy fun. The world has been so shitty recently and this is just something fun and lighthearted to cheer both myself and hopefully some of you up. So I hope you enjoy it!

Dean Smith is a realist. Sure, he likes to read the odd romance novel. But he doesn't actually believe in true love or fairy tales. So when Lydia says they need to talk, he's not expecting this conversation to go anywhere good.

"I can't believe you didn't even ask me, Dean?" Lydia snaps, her voice raised. 

Dean sighs and rubs at his jaw. Downstairs Crowley is throwing a celebration that Jay Gatsby would be proud of. The alcohol is flowing freely. Ladies are laughing while men smoke Cuban cigars and Dean is hiding in the office and fighting with his girlfriend. His whole life feels like it's been in an office these days. It makes sense that this conversation would happen here as well.

"I asked Becky to send you the plane tickets last night Lydia. Please, it would mean a lot to have you here," Dean says trying to sound sincere. He honestly isn't even sure if he wants Lydia here. He's got too much going on to handle her moods. But Crowley thinks having a girl to bring to dinner will humanize him. He thinks that's just because Crowley hasn't met Lydia yet. 

"Oh yeah your secretary, she's great," Lydia says sarcastically. “I see her more than I see you these days, Dean." 

"Lydia..." Dean starts, unsure of what he even wants to say. She’s not actually wrong about that. What can he say, he's been busy lately. Well, more busy than usual. He thought that Lydia, being a businesswoman herself, would understand the job. He thought she’d be more lenient about his long hours and business trips than his other exes. But it seems that was just wishful thinking on his part. 

"Dean I have my own job, I can't leave mid-project to help you schmooze clients. Not that you care what I'm doing anyway." Lydia sighs down the line. "When was the last time we even had a conversation?" 

"Last week, we had dinner together." 

"Yeah with two of your managers, Dean." She scoffs, "Look, maybe we should just finish this conversation when you get back to San Francisco."

Dean loosens his tie, taking a sip from his flat champagne. He doesn’t need to have this conversation later, he’s heard it all before. "No Lydia we should have it now."

"Fine. I'll get my stuff from your apartment this week since you're already gone." She sighs again. She doesn’t even sound mad anymore, just exhausted. Dean wishes that things were different. He wishes that he loved her. That he was capable of being anything other than a corporate machine, but he doesn’t have it in him. He's tried and failed too many times. "Goodbye, Dean." 

"Goodbye Lydia," Dean says and ends the call. 

He stares down at the black screen for god knows how long. The grey background mocking him. He knows the people in his office have photos of their families in the background. Hell, even Crowley, for all his heartlessness, has one of his cars. But Dean's bland and generic. His life is devoid of even a car to love. 

Dean looks out at the spread of party guests in the garden and wonders how many of them are smiling genuinely. Is anyone out there like him, longing for something more in their lives. Probably not. A knock on the door makes Dean look up. He forces a smile when Brady comes in. "Mr Smith, I thought you'd like to know the Cain stocks have dropped another quarter million." 

"Thanks, Brady," Dean says, finishing his champagne flute. He needs to get a grip and get rid of all the existential thoughts in his head right now. “Keep an eye on it for me, I want to know everything that Cain is planning this weekend.” 

“No problem, Sir.” Brady says scampering out of the room. 

Dean stands from the office chair and fixes his tie. He's about to make the biggest deal of his career. He can’t afford to get depressed about his love life. 

Sometimes Dean thinks he's the only one that benefited from the recession. While every other business is going bust. Deans making millions buying their properties and selling them off in pieces. 

Still, he can't help but think Crowley's little shindig is a bit premature. Cain Corporations brought in a lot of business, building ships. For years, it was the gem of the South Bay. Now it’s getting more and more defunct by the day. It’s only a matter of time before the place folds, but Adam Cain is reluctant to sell it to anyone. Even investors. 

Sandover's been eyeing the place for months. Waiting for Cain to cave, and he's finally agreed to talk on his home turf. Forcing Dean to come to the city. Crowley, of course, assumes they are selling, but Dean's not so sure. It's the first time he's felt blindsided before negotiations even started. Cain is more intimidating than anyone he’s taking down before. It’s the riskiest deal Deans tried to make in his decade-long career. For once, he’s not sure if he has what it takes to win. Yet Crowley is celebrating like they've already become billionaires. It would be obscene if Dean didn't know the man for 10 years. He's always been the optimist between the two of them. 

Taking one more look at the celebration outside Dean shakes his head. He’s in no mood to party, but he can always work in his hotel. L.A. isn't his territory, but Crowley insists on keeping a house out here with the stars. He’d probably let Dean stay here but Dean doesn’t practice that kind of masochism. 

Eventually, Dean will cave and buy a house when they get a full building. Instead of the office space, Sandover's currently renting. It would make more sense business-wise. Even if Dean's baffled by this city. He hasn't lived in Sioux Falls in decades, but he’s still a Midwestern boy at heart. Sometimes things stick and his distaste of glitz and glam is one of them, despite his fortune.

  
  
Leaving the comfort of the office Dean realizes Crowley has no such qualms. His place is everything Dean hates about Los Angeles. With its modern art; spiral staircases and chrome everywhere. Sometimes Crowley baffles him more than anything else. They are so different Dean has no clue how they’ve made their business work but it has. Making his way downstairs Dean tries to keep his smile in place. Nodding at some familiar faces and trying to hide from his business partner. He doesn’t need Crowley busting his balls for leaving right now.

He is in such a rush to leave, he almost doesn't notice when he bumps into someone. Smiling apologetically Dean turns and sees Jamie. Because, of course, he needed to meet his ex-girlfriend to really rub salt in the wound. "Jamie, hey," Dean says, trying to hide his insecurities with a smile.

"Hey, Dean!" Jamie says, her smile just as pretty as he remembers. Back then she had just opened her first restaurant, now he's pretty sure, she's made it into a chain. Has it really been that long since they last saw each other? 

"It’s nice to see you." She says like she actually means it. 

Dean clears his throat, noticing her wedding ring. Fuck, that's just what he needed right now. "It's nice to see you too. Congratulations on getting married by the way." 

"Well, Dean I couldn't wait around for you forever." She says laughing brightly. 

God, it's been so long since he’s seen her look so happy. Was she ever this happy with him? Dean doesn’t even want to think about that. 

"Yeah, well, we all know I have the best ass on the west coast if you ever change your mind," Dean says playing into the persona he’s built up over the years. It's not like Jamie's fault he just got dumped. At least he actually got to talk to her in person when she ended things. "Tell me something Jamie, when we were together, did you talk to my secretary more than me?" 

Jamie snorts, "Dean, Becky was one of my bridesmaids." 

"Oh," Dean waffles scratching the back of his neck. This is ridiculous. He thought he put these feelings away in the office. But seeing Jamie has left him spiraling. "Well, thanks for that, I guess. I'll see you around Jamie."

Jamie smiles as Dean flees, straight into parking lot hell. God, he hates this city. He can't prove it, but he’s sure it exists just to fuck with him. Benny sees Dean coming out the exit and shakes his head over the limousine. There’s no way he’s getting that thing out of here until the party’s over. 

He sighs and goes over to the valets. "Hey guys, Mr Crowley said I could take one of his cars to get back to my hotel. Is there any way you can give me the keys?" He says with his most convincing smile. 

The valets look terrified. Crowley loves his cars and puts the fear of God into anyone who breathes near them. There's no way Dean is going to get the keys, but god is he going to try. As if summoned by the valets or, more likely, someone saw Dean leave his party, Crowley appears. With his usual crooked smile in place. No matter how pissed he is, Crowley always manages to look charming, instead of annoyed. It has to be an English thing. Dean can never quite pull that smile off and mean it. "Dean, what are you doing out here? The parties only started?" 

"I have work to do, Crowley," Dean says, avoiding Crowley's eye. "Can please borrow one of your cars and go to the hotel? Benny's trapped until tomorrow by the looks of things." 

"You want to borrow one of my cars?" Crowley asks like Dean asked for one of his kidneys. 

Dean rolls his eyes, "If I wreck it, I'll buy you a new one."

"Or, you could stay until the party’s over," Crowley purrs, he must have someone inside that he wants Dean to meet. He’s always looking for their next deal. Dean wishes he was in the mood to schmooze a client. But right now, all he wants is to bury himself in numbers until the world starts making sense again. He gives Crowley a look. 

"Fine," Crowley snaps, winding down faster than Dean expected. "I've been looking for an excuse to get a mint condition Mazda anyway, something from the 70s." 

“You got it,” Dean smiles, holding his hand out to the valets who look at Crowley for instructions. 

"Give him the Impala,” Crowley says, waving his hand dismissively. “I'm thinking of selling it so it won't be a tragedy when you inevitably wreck it."

Dean chuckles, "I can drive you know," Dean says, pocketing the keys while walking towards Crowley’s private collection. Parked far away from the party guests. 

"It's the black one," Crowley says as Dean walks towards the gleaming behemoth parked at the end of the row. God, his Dad would love this thing. He strokes his hand along the sleek lines and perfect bodywork and aches to put his past to work and pop the hood. He hasn't felt that urge in years, but this car is something else. Dean lets out an appreciative whistle. 

"You remember how to drive a stick?" Crowley asks his smile sharp. He always found it amusing that Dean's father owned a Salvage Yard but Dean gets driven around in a limo. He doesn't seem to realize that, that is exactly the point. 

"The P stands for reverse right?" Dean jokes, smirking a little.

He never actually learned to drive any of his dad’s old beauties. That was always Jo's thing. But he's not going to tell Crowley that. He'll take the keys back without question and Dean needs to get out of here. He's already looking like he's going to blow a gasket thanks to that quip. Dean gets into the driver’s seat before Crowley changes his mind. 

"Don't worry about me Crowley, I'll bring her back just fine." 

Crowley shakes his head, looking no less alarmed when Dean reeves the engine. He thinks he gets why Crowley loves this car so much. "Yeah, sure Dean, do me a favor and don't get lost. You’re not built for the wild streets of Los Angeles at night." 

Dean kind of agrees, but he'd rather gain back all his baby fat than tell Crowley that. "It's the City of Angels Crowley. What’s the worst that could happen?"

“Too much,” Crowley says as Dean drives away. 

\--- L.A.X ---

As far as Castiel's hangover's concerned alarms are the worst thing that's ever happened to him. Sure, his life has been a pile of shit, but Jesus, that thing escaped from the 9th circle of hell.

Groaning, he flips over on the couch and silences the alarm. Blinking at the ceiling and wondering if the water stain looks like Australia or Texas. It's big enough to be either of them. God, Meg's place is such a fucking dump why is he thankful to live here again? Oh right, it’s the only option he’s got. 

Castiel glares at the stain some before trying to get his shit together. His stomach lurches. His lunch of pizza and pity rum churning in his stomach. So maybe trying to eat and drink away his pain was a mistake. It’s not like he knows any better coping mechanisms. 

Getting to his feet Castiel deals with the trash and tries not to look too at the rejection letter on the table. That's the reason he's in this position in the first place. 

Applying to college had been a dumb idea, to begin with. Castiel barely finished high school for crying out loud. At the time it didn't matter. Not when his dad had Castiel’s whole life all mapped out. Now, though at twenty-six, he's one step above homeless and selling himself on the streets. His father would be so proud. 

Castiel snorts at the thought and sticks his head into Meg's room. Clothes are thrown everywhere, but Meg’s not buried underneath them. Which means she’s left without him. Again. 

Shaking his head Castiel stumbles into her bathroom and brushes his teeth. No doubt, Megs at the club because Meg is always at the club. He wonders if she saw the letter when she was leaving. Knowing her, she noticed it and the half-empty bottle and figured Castiel didn't want to talk about it.

Meg would say he's being unrealistic anyway. Which is why he hasn't told her yet that he's looking at colleges. He knows he won't be able to ignore the heartbreak if she tries to comfort him. He figures Megs already worked it out. She's always been way smarter than anyone would assume at first glance. If she ever got clean Castiel has no doubt she would do something amazing. But it's not his place to lecture her, not when he's just as much of a mess. 

He just hopes she's clean enough to work tonight. He hates standing in the corner by himself. Castiel’s still too new at the job to pick up clients the way Meg does with ease. At least getting ready has gotten easier. He can’t afford to miss prime-time on the Boulevard by feeling sorry for himself. 

It's not like he’s living a bad life. The apartment's shit but it’s his own and Meg far outshines his family. Sure, this wasn’t his life plan, but he's mostly happy. Besides his job isn't as awful despite what everyone may think. He just wants more from life than what he's got. He likes fucking but he doesn’t want it to be his job forever. 

Before he started he was always a sexual person. He happily went with anyone that caught his eye. But being a hooker is nothing like having one-night stands. Castiel isn't out to have fun. He’s out to make money. He had to learn how to do it right. How to look like and be a fantasy worth paying for. 

Meg had never trained a guy before they met so it took some time to get the look part right. Castiel may have been younger then, but he was too beefed up to pass for a twink. Similarly, he wasn't big enough to pull off the bear angle. It took weeks of raiding Santee Alley before they worked out he should lean into both aspects.

He has a small collection of cheap shirts. Some lace, others so chiffon they are transparent. Shorts so tiny it's obscene. A kilt that he loves and the faux-leather pants that Meg says make's his ass look amazing. He puts those on with one the white shirts. And tries not to fidget in the mirror.

He feels more like a pirate in some purple banner novel rather than a hooker on the streets. But it’s not a bad look and it’s not like Castiel cares what type of clients he picks up. Maybe tonight he'll seduce a nice cougar instead of his usual fare. Shaking his head at his reflection. He scoffs and grabs Meg's eyeliner and his heeled boots as well. Wondering how he can make a pirate fantasy play out. Does he need to stop by Guy's place and get a net? How would that even work?

Lost in some vaguely terrifying thoughts he grabs his bag and locks up. His heels clicking on the walkway. He hears Richard before he sees him, giving some new guy his usual rent or else lecture.

“Shit,” Castiel curses under his breath. Richard is a real dick about getting his rent on time and Castiel doubts Meg paid him before she left.

Cursing up a storm, he sulks back into the apartment and reaches for their emergency stash of cash. Of course, the box is fucking empty. Why wouldn’t it be? It’s not like his day has been going well or anything. If they get evicted he’s going to kill Meg. Castiel contemplates getting his stash of hospital cash hidden inside the couch. But they aren’t that bad yet. Worse comes to worst Castiel can suck Richards dick again and buy them another week. Fighting down a shiver at the thought, Castiel puts the box back in the cistern. 

There's a chance Meg hasn't spent everything yet, maybe they can earn back the rest of their rent tonight. Until then, he’ll have to sneak out the fire escape. Its feat in heels, but Castiel has done it before. His neighbors glare’s at him for doing it again. Castiel gives her a reassuring smile, but she keeps glaring and smoking out her window. He shakes his head at her and jumps to the ground walking to the hole in the fence without another look back.

The streets are as busy as usual, but Castiel keeps his head down for a change. Normally he wouldn't be against a little flirting if it leads to getting some cash. But he has to find Meg first, so he knows if he needs to charge extra. If Megs spent it all, she’s going to be cleaning the bathroom for a month. That’s if they don’t get evicted first. If that happens he might genuinely kill her. 

He's close to the club when he notices the police cruiser. Swallowing Castiel walks between the crowd, trying not to react to the body in the alley. A detective stands beside him, questioning some guy that looks like he's got a hit of the good stuff. "What do you know about that girl?" The detective asks as Castiel tries to catch a glimpse of the corpse's face. 

The Tweaker sighs, looking offended by the question. "I'm telling you, man. I don't know. I don't even know who she hangs with." 

Castiel frowns as does the detective. "C'mon, man. We just pulled her out of a dumpster in the back of your building. Who was her pimp?" The detective asks as if he actually cares what happened to her. Castiel doubts that. It’s probably just close to the end of his shift. Castiel sighs as the body guys tilt the girls head and Castiel gets a glimpse of blonde hair. He sighs in relief, it wasn't Meg then. 

The Tweaker scoffs, "Cocaine was her pimp. She's a strawberry. She is out on these streets day in, day out. Tradin' her sorry self for some crack." 

Castiel raises his eyebrow at that one, noticing the black staining his teeth. He wonders how much it pays to be a hypocrite these days? He walks away as a group of tourists breaks through the tape. Taking pictures of the body and the cops like it’s a scene from CSI. God, this city is a fucking mess. 

He walks across the street to Seraphim and for once doesn’t scoff at the name. Balthazar thought he was oh so clever naming his scummy L.A. bar after a choir of angels. Like the idea was so original. His fucking ego makes the A-listers look modest, but the club is cheap and doesn’t ask questions. Meg of course adores the place for that simple reason. 

As usual, the places packed with people grinding together on the dance floor. He doesn't see Meg's dark curls anywhere. Grumbling under his breath, he walks up to the bar, waving at Zeke and yells over the thumping bass. "Hey, Zeke have you seen Meg?" 

"She's in the pool-room," Zeke says with a scowl, which means Meg is definitely here and being her usual self. 

Castiel gives him a thumbs up, climbing the stairs to where Meg is dancing in the corner with a joint in her hand. She almost drops it when she sees Castiel. "Clarence, you made it," She says, trying to smile innocently. Her eyes are red-rimmed and there's vodka on her table, but for her, that's sober. "Guys, you know my roommate Cas, Cas this is Casey and that's Rachel -" 

Castiel scowls cutting her off, "I know everyone here Meg. Where's the rent money?" 

"Well, you see, I kinda threw a party, Balthazar sold me some great shit and -" 

"Meg please tell me you didn't spend all our rent money on drugs?" Castiel asks desperately, trying not to shake her. He loves her like family, but she's so reckless sometimes. 

"I needed a pick me up, Clarence. You know I had a bad week." She's pouting and Cas tries not to react.

She did have a shit week. The guy she brought to the Plaza had tried to skimp out without paying. Fucker got physical when Meg confronted him about it. Meg, long past a rookie, brought her knife and used what Castiel had taught her to fight back. So the guy paid up, plus interest, thanks to a slice in the thigh. Still, Meg was pretty shaken up after. 

Castiel feels bad for her. But he’s still pissed that she stole his half of the cash without checking with him first. He likes to make contingencies when Meg plans on going off the rails. He worked too hard for that cash to wind up homeless. "I can't believe you took it while I was sleeping." 

"You were unavailable for consultation." She says avoiding his eyes. Castiel raises an eyebrow. “Alright, alright I’m sorry I’ll wake you next time.” Then, with one last toke, she passes Castiel the joint as a consolation prize. 

He takes it and inhales, trying to calm down. "We gotta get more guys tonight. Dick's been parading the halls."

"You could always come and stay with me Castiel," Balthazar purrs. Throwing his arm around Meg's hip. Castiel rolls his eyes and takes another hit. 

Meg bats Balthazar's hand away, "We're doing just fine on our own Bal. C'mon Angel we got shit to do."

She grabs Castiel's wrist, pulling him towards the staircase. People raising their eyebrows at them. They see Meg with her tiny skirts and low cut tops and never imagine the strength she has underneath. He stumbles along behind her laughing despite himself. The stuff she bought is actually pretty good shit, but Castiel would still prefer a roof over his head.

"I thought we were going to the corner," He says as she tugs him towards the bar instead. 

Meg rolls her eyes. "We are but snacks first." She starts gathering oranges slices and cherries into a napkin. "I am sorry about the rent Clarence, but it is my apartment.” 

Castiel scoffs just as Zeke slaps Meg's hand away from the fruit. "This ain't a buffet, Meg," He says, ignoring her as she flips him off. 

Putting her stolen fruit into her bag, Meg struts to the door and away from Castiel, a smirk on her red painted lips. Castiel waves at Zeke and takes one last hit before putting the blunt out with his fingers. No matter how good this stuff is. He's still not sure he's going to make it through the night without blowing a gasket. He chases after Meg. 

"Yeah, it's your place, but I live there too Meg. Some of that was my money." He says bumping her shoulder as he falls in line. They pass the body van going up the street. "I'm not ending up out here again." 

"Okay, your right, I’m sorry. But don’t worry Clarence, we'll be fine. Balthazar keeps bugging me about you. I had to distract him with something before he tried to scout you again." She sighs, walking down the Boulevard with a sway in her hips." You ever think we should just give up and give in to him? He’s really into you." 

"No, You know Balthazar, he'll run our lives and take our money," Castiel says, his hands in his pockets. He looks down at the stars on the ground instead of meeting her gaze. The thought of being Balthazar’s own personal fuck toy makes him more nauseous than he’d care to admit.

"Yeah, you're right," She says, smiling at him, the same soft way she did on the night they met. Castiel feels his anger melt away. He can never stay mad at Meg for long. She’s done too much for him. "We say who, we say when, and we say how much. No complications that rule number two." 

Castiel shakes his head fondly. “You with your goddamn rules."

"Yeah, yeah, you love them." Castiel rolls his eyes stopping in front of their usual bodega. Meg's smile goes sharp when she spots a woman in stilettos leaning against a tree outside it. "Speaking of rules," Meg says, a glint in her eye, "Hey, Ruby." The girl lifts her head. Her dark curls styled like Megs. "You see the stars on the sidewalk, Hun?" 

"Yeah, and? What’s it to you Meg?" Ruby says, straightening as Meg talks to her. Castiel bites his lip, trying not to laugh, anyone on these streets should know now to try to pick a fight Meg. She'll always win and she usually fights dirty.

Laughing falsely Meg taps her heels against Bob Hope's star. "Yeah, well, read the names doe eyes. Cas and me, we work Bob Hope, we work the Ritz Brothers, we work Fred Astaire, we work all the way down to Ella Fitzgerald. This is our turf. We got seniority. You better get off our corner." 

"I was just resting Meg. Besides, he's still new," Ruby says, giving Cas a condescending look that would put Zeke to shame. 

"Do I look like I give a shit, you want a rest, you best go back to Monty Hall or Esther Wilson. -"

" - Williams. -" Castiel says breathing a laugh. Meg is always so fucking feisty when someone's on her turf. 

"- Esther Williams! Where you belong!" Meg yells, smirking as she shoos Ruby away with her hand.

Ruby huffs her heels clicking on the pavement. "Yeah, whatever you’re such a bitch Meg." She yells over her shoulder.

Meg pouts, taking Ruby’s spot against the tree. "Am I really a bitch?" 

Castiel pinches his fingers together, "A bit." He says, laughing when Meg hits his shoulder. 

"Yeah, whatever you say. Maybe I'm just hungry because someone got drunk and ate all the pizza." 

Castiel shrugs, the weed making his limbs feel lighter. He doesn't even feel all that upset about his rejection letter and the rent anymore. They can make it up again tonight easy. "I'll keep a slice for you next time." 

"Yeah, yeah, whatever Clarence." She scopes out the cars frowning when nothing stops. "It's looking pretty slow tonight." 

Castiel sighs stretching his arms over his head. "We'll charge double, not like they'll notice." Meg laughs, her eyebrows raising as she looks down the highway. From behind him a car engine purrs and coughs. Almost hitting the curb. 

Meg smiles, taking in the gorgeous vintage and sees dollar signs. "You take this one angel, see if you can score some rent money."

Castiel swallows and sticks his hands in his pockets. He’s always more nervous with the rich guys. "You sure you don’t want him? He looks like he's got cash to burn."

"Yeah, but it wasn't my flexing that got his attention," Meg says smirking. "Don't take less than a hundred. Call me when you're through and take care of yourself."

Castiel rolls his eyes and straightens. For all her faults Castiel doesn't know what he would have done without this woman in his life. "Take care of yourself." He says strutting over to the car. Allowing the heels to lengthen his gait.

"Yeah, that’s it, work those muscles that Uncle Sam gave you!" Meg yells after him. Castiel shakes his head, ignoring her as he gets closer to the car.

Leaning with his arms against the window frame Castiel gives his best flirty smile. Blinking in surprise at the guy's handsome face and bright green eyes. "Hey, stud, you lookin' for a date?" 

A small flush darkens the man's cheeks clashing adorably against his red tie. "Ah - no," He says in a honeyed drawl. Castiel licks his lips drawing the man's attention to his mouth. "But could you give me directions to Beverly Hills?" 

Castiel sighs. Of course, the first attractive person he’s seen in months is only looking for directions. "Yeah, I could," Castiel says with a smirk. It's not the guy's fault he's so gorgeous, but Castiel feels like repaying that tease with one of his own. "But I'll only tell you for five dollars." 

"That's ridiculous." Green eyes huffs. Shifting the gear stick with great difficulty. 

Castiel rolls his eyes, "Well, for that the price went up to ten." 

"You can’t charge ten bucks for directions," Green eyes says, still trying to get the car to reverse.

Castiel shakes his head, unsure why the guy is being so difficult. With a suit like his, it's not like ten bucks would be a hardship. "I can do anything I want to stud. I ain't lost.”

Green eye's groans, but Castiel ignores him. Turning around so his ass is in the window frame. He’s at the perfect height to watch the man's face in his side mirror. His eyes are glued to Castiel's ass. Which is what Castiel was hoping for. 

"Fine, alright, fine, you win." Green eyes say swallowing heavily. Castiel turns around, leaning down again with a warm smile. The man frowns. "Have you got change for a twenty?”

Castiel raises his eyebrow considering his options. The guy's interested in him. There's no arguing with that. So it's probably the hooker thing that's got him so on edge. Castiel knows all he needs is time to wear him down. Smirking Castiel opens the car door and gets in. 

"Hell for a twenty I'll show you the way in person. I can even show you where all the stars live if you like.” The guy gulps but doesn't say anything while Castiel gets comfortable. Fuck, he's even prettier up close. If Meg didn't spend their rent money Castiel would give him a discount.

"It's okay, I already saw Tom Cruise's place." The guy scratches his bottom lip, looking down at Castiel. His eyes lingering on how Castiel’s pants stretch over his bulge. He licks his lips. 

"Well, I can't top that now can I," Castiel says, smirking when the guy actually looks up at his face again. Even in the low light, he can see freckles under the guy’s blush. Oh, Castiel is so getting laid tonight, it's only a matter of time. 


	2. Chapter 2

**Notes for the Chapter:**

> Well if you are following me on tumblr you will know that I changed the updates from every Wednesday to every other Wednesday because the word count for this is ridiculous. Seriously doing two POVs is such a fun way to write this but also I'm at 10 k and this is chapter 2. 
> 
> Saying that I hope you like this update, I had fun writing all the banter in this, Dean Smith and Endverse Cas are just so interesting to play around with.

Normally Dean is never this stupid. He never takes risks, but tonight is shaping up to be a wonderful experience altogether. First, he gets dumped, and then he goes and gets lost. Because of course, Crowley wouldn't install a Satnav in his classic cars. What’s worse is no one seems like they want to help him. He knows he’s not exactly in the best parts of town, and he's looking to get to Beverly Hill’s for Christ's sake. He knows that screams rich prick. Honestly, when he was younger, Dean would have messed around with someone like him as well. So the hobo telling him his box was Tom Cruise's place, while rude, kinda makes sense. What totally doesn't make sense is the guy currently hogging up his passenger seat. 

Who just decides to trust strange men and let them into their cars? Dean Smith apparently. He's going to get robbed, it's only a matter of time. But fuck it might be worth it. He actually thought he had a pretty good grasp of the car. Until he turned down that last block and saw the guy on the corner. Stretching his broad back and showcasing one of the coolest tattoos Dean’s ever seen. Angel wings perfectly inked down the guys back. The dark feathers dipping down into the waistband of goddamn leather pants. Dean’s only human, of course, he fumbled the stick shift and put the car in park. He's not a saint, but he didn't exactly plan to buy what the guy had been selling. Then the fucker had offered to take Dean to his hotel and Dean was powerless to stop him. 

It's not like Dean doesn't recognize a hustle when he sees one. He's been on the other side often enough to know the tricks, and it's not like Dean's staring had been subtle. He's sure the guy thinks he can talk Dean into spending some more time with him. And Dean’s not sure he would exactly mind. Dean’s never paid for sex in his life, but he's gotta admit, after the night he's had, it's got some potential. Hell, right now he's doing a better job of watching his new companion than he does the road. He can't really help himself. It's been so long since Dean's been with a man, outside of his fantasies anyway. So of course, he's rendered stupid by this guy. He's exactly the type of man Dean slept with back in college. Which maybe wouldn't be so bad, if this guy wasn't also a sarcastic hooker that conned him out of twenty bucks. If it got out that Dean slept with a hooker, especially a _male_ hooker, his stocks would plummet. But Dean still can't help himself from thinking about the guy's mouth. 

Shaking his head to clear away the dirty train of thoughts. Dean focuses on driving except they come to their fifth ( **_Fifth_ **!) jerky halt. Fuck this guy is making Dean nervous. 

"Did you steal this thing or something?" His companion asks, a crooked smirk on his stupidly handsome face. 

"Something like that," Dean breathes out a laugh, thinking of Crowley's face when he took off. "It's my friend's car, I'm borrowing her, but I doubt she's ever had a tune-up in her life." He lifts one of his hands off the wheels to scratch his neck. "Or it's been way too long since I've handled a stick shift."

The guy's eyes darken, and Jesus, Dean doesn't think he's ever seen a blue like that in his life. "I'm going to do you the favor of not making the obvious joke right about now." He says and fuck, even his voice is tailor-made to fit Dean’s kinks. 

Dean flushes when the dirty implications of what he just said, hit him like a smack to the face. "I - ah didn't mean - God - get your mind out of the gutter dude."

"The gutter is kinda my job description." The guy jokes, gesturing down to his whole body. Thankfully, they are actually at a red light this time. Since Dean's focused on everything but the road. Those pants are something else. The guy licks his lips. "But I'll stop with the jokes if it offends your delicate sensibilities." 

Dean rolls his eyes and turns back to the road. He needs to get his shit together. He's not some blushing virgin. "Don't change yourself because of me, man. I'm not used to people making innuendos anymore. HR doesn’t approve of that kind of thing and I'm hardly out of the office these days."

The guy snorts, "I wasn't aware people actually said the word innuendo in real life." 

"Is this your sales pitch, insulting me?" Dean asks, more amused than he'd like to admit.

"Why? Is it working?" The guy asks, raising an eyebrow and _oh boy_ Dean needs some air. 

Lowering the window Dean clear's his throat. It only takes another handful of seconds before he almost sends the car into the curb, he course corrects. The guy, faintly chuckling beside him. Has he ever successfully flirted with someone in his goddamn life? He can't remember. Fuck this guy is messing with his head. "What's your name anyway?" 

"Whatever you want it to be, baby." He says smirking at Dean. Dean shakes his head wondering if that line usually works for him. 

"Cas." He says quickly, a little too quickly in Dean's opinion. He steals the guy's move and raises his own eyebrow. The guy licks his lips, "Fine, it's Castiel." 

"Your real name is Castiel?" Dean asks because, seriously? That sounds made up. 

Cas rolls his eyes, "Yes, it is. Do you want to check my driver's license? Which I have by the way, unlike some people in this vehicle." 

"Hey, I can drive." Dean protests as the car jerks again. " -An automatic." 

Cas chuckles, a deep gritty sound that gets Dean’s insides hot. He clears his throat, "What do you prefer? Cas or Castiel?" 

"Cas is fine," Cas says, still smiling at Dean. "I know my name can be a bit of a mouthful."

Dean - a forty-year-old stoic CEO - giggles like twelve-year-old saying boobs for the first time. "Now who's setting up the innuendos?"

"I only state the truth. It's a comment I've heard a lot." 

"I'm sure you have," Dean says staring down at where the guy's package is straining against the leather. Fuck he is not making it out of this car alive.

Cas’s eyes darken watching Dean watch him. "Okay, you'll want to take a right up here."

Dean sighs trying to turn when the gears grind again. He pulls the car into the curb thumping his head against the wheel. "Hey Cas, how do you feel about driving an Impala?" Dean asks figuring he might as well go all out on the stupidity tonight.

"You want me to drive this thing?" Cas asks looking down at the car with a genuine light in his eyes. It shouldn't be as adorable as it is. 

Dean licks his lips, "Yeah, why not? Are you turning me down?" 

"Never," Cas says, his voice getting impossibly lower. 

Dean shakes his head and gets out of the car. Letting the fresh air clear his brain a little. It's a lot less intoxicating than whatever cologne Cas has on him. He watches as Cas slide's across the bench seat and gets into the driver’s side. Fuck, he hasn't felt this riled up since his teens. He needs to get a hold of himself before he does something stupid. Like, end up in the tabloids for public indecency stupid. He takes another deep breath and gets back in the car. Castiel turns the key admiring the engine as it purrs for him. 

"You should really learn how to drive this car." He says seamlessly shifting the gears, so she glides back into traffic. 

Dean watches him, finally free to give Cas his full attention. "You make it look pretty damn easy."

"I make a lot of things look easy."

Dean shakes his head and laughs. "God do you have like a joke book written up or something?" 

Cas tilt’s his head, "Why? Do you think it would be a bestseller?" 

“Maybe,” Dean chuckles and pulls at his tie. "Hey, speaking of money, how much do you guys make these days anyway?" He says trying for casual and missing by a mile. 

Cas smirk widens into a full-blown grin. "A hundred bucks." 

"A night?"

"An hour."

"You make a hundred dollars an hour and you're taking a break to give me directions?" 

"This isn't a break, you gave me twenty dollars," Castiel says smirking again. 

Dean shakes his head, holy shit, he thought he was a good businessman. "Yeah, I suppose that's true. Still, that's pretty stiff."

Without even pausing for breath, Cas reaches over the gears and grips Dean through his pants. "Not yet, but it's got potential." He says like what he did is no big deal. 

Dean whistles through his teeth. _Holy_ . **_Shit_ **. He doesn't know if he should get turned on or offended. Looking at Cas's smirk he's ashamed to admit the horny part of his brain is winning. Damn this guy is good. He is still gaping as Cas pulls up at the hotel. 

Cas lifts his hands off Dean's dick. Just in time, as a valet appears at their sides. “Good evening, Mr Smith. Will you be using the car any more tonight?"

"No, ah, no thanks bud. Not tonight." Dean says, blinking away his shock and stepping out of the car. Willing his half chub to retreat before anyone sees it. Cas smirks at him, passing the keys to the valet. 

Dean looks up at the building then back at Cas. "What are you going to do now?" Dean asks, licking his lips as he looks Cas up and down. "Take a cab back to your office?"

Cas ducks his head and chuckles. "My office, I like that." He puts his hands in his pockets and shrugs, "But yeah I'll get back there eventually. I’m more surprised we both got here in one piece. You're driving had me worried there for a second."

Dean rolls his eyes, "Yeah, yeah at least we made it." He clears his throat again, pointing back at the hotel. "I should get in there. I have some work I've got to do," He says and immediately regrets it. 

Cas's smile fades. "Yeah okay, I understand, guess I'll be heading back to work, too." He says pressing a chaste kiss to Dean’s cheek before strutting away. "I'll see you around Mr Smith." 

Dean presses his hand to his cheek and looks back at the hotel. It's stupid to think about Cas any longer. He can finally put tonight behind him and get some real work done. That's what he came to this godforsaken city to do. He sighs and starts walking around the corner instead. He spots Cas, sitting on the back of a bus bench. His heeled foot kicking the side. Dean stares at him and considers his options and realizes only one of them is truly appealing. "I thought you were getting a cab?" He says, appearing at Cas's side. 

Cas raises an eyebrow, his foot thumping again, making the bench rattle. "Yeah well, I like the bus."

"Oh," Dean says, leaning into Cas's side. It's too late to back out now. "So, A hundred bucks an hour, Huh?" 

"Yeah," Cas says staring at Dean from under his eyelashes. 

Dean swallows and straightens his tie. "Okay," he holds out his hand, "Well would you like to join me for an hour, Cas?"

“It would be my pleasure,” Cas smiles, hopping off the bench to stand beside Dean. 

Dean looks at his lightly haired chest then around at their companions on the street. "Hang on, we can't have you walking through the lobby looking like Fabio." He says and starts fastening up the buttons.

"You get it's a transparent shirt, right?" Cas asks, swallowing as Dean's thumb strokes a line down his throat. Relishing in the stubble starting to grow there. He's always been into the beard thing. 

"Yeah, I noticed," Dean says, glaring at Castiel's nipples. "Still I’ve got to try something."

"Well, then I appreciate you trying to protect my modesty, Mr Smith." 

Dean breathes out a laugh, "Dean, if we're doing this, please call me Dean instead of that Mr Smith, crap." 

"Dean huh? Funny Dean’s just about my favorite name."

Dean rolls his eyes at the obvious line, stepping out of Cas's personal space. "Hardy-har you've already made your sale Cas. Now come inside."

"I only do that for two hundred," Cas says with a straight face, his eyes twinkling.

"Cas!" Dean yelps, looking around to see if anyone heard him. 

Cas chuckles again. "What? That was a good one." 

"Yeah, it was," Dean reluctantly nods and holds out his arm, "Now are you coming or not." 

Cas's eyes darken. "Well, that's really up to you, isn't it?" 

Dean damn near swallows his tongue. Okay, there's no way he's making it through tonight without losing his mind. 

Inside the lobby, Dean tries to keep a level head and a modest situation below the waist. He may hate L.A. but he likes this hotel. About six years ago Sandover acquired an intern to shadow Dean for his management degree. Dean had been grumpy about it at first, but Sam Wesson had been pretty awesome. Now he's the concierge of this place. He always gives Sandover employees a discount. Which is just as well, because even with his wage packet, this place is ridiculous. Dean always tries to be on his best behavior when he comes here. Well until tonight at least. 

Cas sticks out like a sore thumb among the suits and silks. People are staring at him; which Dean thinks is a little unfair. He knows a lot of celebrities that wear outfits like Cas's, and they definitely stay in places like this. Yet, these guys are looking at him like he's a freak. The part of Dean that grew up poor, rails against it. Crowley has spent a decade trying to iron that part out of Dean. He can't risk Dean offending someone that may be good for business later. Thankfully, it's one of the few of Crowley's lessons that has never stuck. Dean diets, he wears designer suits and rarely drinks, but he never stands for smug pricks. Despite the scrutiny, Dean wraps his arm around Cas's waist and guides him through the crowd. 

For once, he doesn't care about the fact that it's obvious they are together. He's spent years shoving himself back into the closet, for his job, but tonight is different. For once in his whole career Dean's taking the night for himself. Cas somehow seems not to notice the attention on them. Either that or he doesn't care. He walks with his head held high. His heels clicking like gunshots on the marble floor. Dean strokes his thumb against his thick waist. Feeling the warm skin beneath his palm and relishes in pissing off some douchebags.

Knowing Crowley, he started blowing up Dean's hotel phone the second he turned his cell off. So, he makes for the front desk first. Cas is staring at the chandeliers with a look Dean recognizes from his own face. It takes a long time to get used to this kind of opulence. Thankfully, the night shift concierge isn't Sam. Who would definitely question why Dean was with someone like Cas. Instead, the pretty redhead blinks at them, giving Cas a polite once over but doesn't comment. "Good evening, Mr Smith."

"Hey ah - “Dean ducks his head looking for a name tag, "- Anna. Do you have any messages for me?"

"Yes, we have several. " She opens a thick ledger and glances down at the pages. “I'll fax them up to your room." 

"Thank you, Anna."

"Will that be all, Sir?" 

Dean almost says yes, but hell, if he's being reckless tonight, he might as well do it in style. "Um, no, actually could you send up some champagne and strawberries, please?" 

Cas, of course, raises an eyebrow at the request but keeps his mouth shut. Dean imagines he's not used to this kind of treatment. Dean doesn't usually dole it out either, but he's in the mood to pretend. Just for a night. That he isn’t the corporate robot but the romantic he keeps buried beneath it.

The redhead nods and Dean gives her a simple wave as he escorts Cas to the elevators. "Why aren't you just the old romantic?" Cas quips the second they are out of earshot. 

Dean ducks his head, avoiding Cas's gaze. "What? Can't I do something nice."

"Of course, you can, it's your money. You can do whatever you like." Cas says and just like that Dean remembers this isn't a fucking date, it's a transaction. He almost pulls his arm back, but then that would make things awkward. If Dean only has Cas for an hour, he wants to enjoy it. Fuck, why does this have to be so complicated? 

Sweating a little, Dean almost disregards the other couple in the hallway. They are older and probably Christian judging by the giant gold cross around the wife's neck. They give Dean a judgmental glare he hasn't seen outside the bible belt. Dean smiles at them, daring them to make some kind of remark, but they just stare. Faces the very picture of polite disgust. 

Cas glances at them, then at Dean with a glint in his eye. "Oh, look hon, my shoelace has come undone." He says, then lifts his leg placing it a trash can. Slowly he bends over, folding himself in half to look at his shoe. Fuck, Dean can see his muscles rippling under his shirt. The angel wings shift, and Dean follows the feathers down to his ass. Which yes. That's definitely worth a hundred dollars an hour. Possibly more. Dean swallows, his throat dry. 

Cas laughs, "Oh I forgot these boots don't have laces." He says planting his foot back on the ground as if he didn't just put on the show of a lifetime. 

So, Cas has noticed the attention after all. Dean bites his lip to hide his grin. _Jesus Christ_ , the woman is clutching her cross. The elevator opens, revealing the operator who stutters when he sees Dean. "Good evening, Sir." The guy says not meeting his eye. "Penthouse, right?" 

Once again Cas raises his eyebrow as if he has any right to judge after his little display. "You are just full of surprises, aren't you?" he asks, stepping into the elevator without a care in the world. 

Dean shakes his head and follows him inside. “Your one to talk.”

“Oh Stud, you have no idea,” Cas smirks, leaning into Dean's side as the elevator doors close on the couple outside.

\--- L.A.X ---

Castiel knew Dean had money, buts it not until he steps into the penthouse that he realizes how much. The place could fit Castiel’s apartment inside it and have space for Seraphim’s pool room as well. The walls are white with detailed crown moulding that he knows cost's a pretty penny. The furniture is dark in contrast, wingback chairs, a desk and full-screen TV. He can already see rooms branching off from this one. Which means this place has more rooms than his apartment as well. 

Surprisingly, thick pink carpet covers the floor, so soft his heels sink. It somehow doesn't fit in with what little he knows about Dean. Dean is the very picture of rich masculinity, and this carpet is anything but. The contradiction helps him relax. The lobby, with its high chandeliers and marble flooring, had been hell. Every eye was watching him. Judging him for daring to enter their world. He assumed Dean would reprimand him from his stunt downstairs. But if anything, he had looked amused. Now he stands in the doorway. Watching Castiel take in his space.

"Do you like it?" Dean asks in that honeyed draw that melts Castiel’s insides like butter. 

Seeing him in the light Castiel is struck by how gorgeous his client is. He has good strong shoulders, highlighted by the cut his suit. A slim waist and an ass firm enough to give Castiel a run for his money. His sandy blonde hairs slicked over to the side. Castiel’s fingers itch with the need to mess it up. "I've seen better." Castiel lie’s walking towards the open balcony door and away from Dean before he does something stupid.

Dean makes a humming noise that Castiel is to distracted to hear. He's never seen his city look so beautiful. "Well I'll give you one thing; it’s got a great view." Castiel says looking over his shoulder at Dean. "I bet during the day you can see the ocean." 

Dean chuckles, rearranging some papers that seem to have come out of his fax machine. "I'll take your word for it. I don't go out there." 

Castiel frowns walking back into the room to stare at Dean. "Why not?" He asks, puzzled about why someone would have this skyline and not waste spend hours watching it. 

"I'm afraid of heights," Dean says distractedly. Flicking through some of his papers again. Castiel throws his bag down on the couch, wondering if this is really how Dean wants to spend his hundred bucks. 

"Why did you get the penthouse then?" He asks instead, leaning back into the chair to show off the goods. 

Dean looks up, his cheeks flushing, "Ah - Because the penthouse is the best and I like the best." 

Castiel raises an eyebrow, strutting towards Dean who is finally watching him again. Sitting on the edge of the desk, Castiel smiles. "I guess that’s why you picked me then,"

Dean shakes his head, a breathless laugh escaping him. Castiel likes it when he laughs. The creases around his eyes are endearing. "I'm going, to be honest, Cas. I have no clue why I picked you up. I hadn't exactly planned this." 

"Well, do you plan everything?" Castiel asks gripping Dean’s tie. The thick red silk sliding against his palms.

Dean swallows, "Usually, yeah."

Castiel looks up at him and tilts his head. Fascinated as Dean's expression softens. "You have never done this before? Have you?" He says in disbelief.

Meg had insisted that rich guys always look for whores, just not usually on the Boulevard. It's why they used to go to Rodeo Drive sometimes. At least before the police patrols got tighter. He had thought Dean was nervous because of _where_ they met. He never thought that Dean might be new at this. What kind of rich guy doesn’t spend his money on an escort? Dean really is full of surprises. 

"Ugh - no," Dean says, his cheeks reddening. "I mean I have slept with people before. Both women and ah men. But no - not this."

He's adorably flustered and for once Castiel wishes the situations were different. That Dean was just a hot guy he could ask on a date, but that’s not how it is. He sighs. "Well, you know, you could pay me. That's one way to break the ice." 

"Oh of course," Dean fumbles at his pants, pulling out a wallet thick with bills. "I assume cash is acceptable." 

"Cash is good," Castiel says, releasing Dean’s tie to put the bill inside his right boot. He smiles and crosses his legs so he can unzip his other boot. His condom stash falling into his hand. "Okay, now you get to pick one. I got red, I got green, I got yellow. I'm out of purple, but I do have one gold circle coin left. A rich guy like you, you'll probably want that one." 

Dean clears his throat, stepping back from Castiel’s hands and fixes his tie. "Look, why don't we just talk for a little first, okay?" He says stumbling backwards over to the couch. 

Castiel raises an eyebrow. "Talk. Yeah... uh... okay." He says, rubbing sweaty palms on his pants. He's never had a John ask to talk before. Which is great, because Castiel is painfully bad at small talk. Dirty jokes; fighting techniques and the best places to get a condom. Castiel's got those topics covered. But small talk? That’s not in his skill set. "Well Dean, are you in town on, uh, business or pleasure?" 

Dean sits on the couch, tapping a staccato on the arms. "Business, I think." 

"You think?" 

"Well, tonight isn’t business, right?" He asks, still tapping. 

"Not for you, no," Castiel says making his way over to Dean’s personal space. Dean watches him with wide eyes. Castiel has never met a client who lets a hundred bucks go to waste like this. He sits himself down on the footstool and puts his hands on Dean’s spread legs. Letting Dean see what he’s missing right now. 

"Well let me guess. Most of the Hollywood bigwigs have their own places round here. So, are you some kind of lawyer?" He whispers into his ear, trying his hardest to make his question sound seductive. 

Dean shakes his head, smiling nervously as Castiel rubs his knee. "No not a lawyer."

"Hmm -" Castiel pushes his hand higher, sliding up Dean’s thighs. "- well how about a banker?" 

Dean swallows, his eyelashes fluttering as Castiel reaches his waistband. An awful ringing noise interrupts the moment. Castiel stands and so does Dean. They both look at the door, then back at each other. Dean licks his lip and Castiel suddenly aches to taste it. The ringing comes again. 

"What was that?" Castiel asks, still looking at Dean’s mouth. If Castiel wasn't wearing heels, Dean would probably be a little taller than him. He looks a bit older too, if the lines around his eyes are anything to go by. Fuck he's handsome.

"Room service," Dean says licking his lips. Castiel closes his eyes trying to resist the temptation of Dean’s mouth.

He shakes his head, "Might as well make myself useful. Take a load of Stud." Castiel pushes Dean’s shoulders so he falls back onto the couch. Rasing an eyebrow when Dean's green eyes turn darker than jade. He forces himself to turn around and not sit in his lap.Fuck Dean is beautiful and so, so dangerous.

He walks to the door, Megs voice ringing in his ears. He can still see her sitting outside the dressing room while he tried to find the right look.

_"Now listen closely angel," She said serious for a change. "Rule number one for this gig. None of that intimacy stuff. You’re not their boyfriend. So, don’t go kissing them on the mouth, or catching feelings for your regulars. It's bad for business."_

He thought it was a stupid rule for years, who would fall for a John? But looking at Dean, laid out like all his wet dreams come to life, it makes a lot more sense. He takes a steadying breath and opens the door. A man steps in with a tray, giving Castiel his third surprised once over for the night. Dean clears his throat. Glaring at the man, who straightens, “Good evening,” He says to Dean and only Dean.

Castiel rolls his eyes, “Yeah hello.”

The man blinks at him, still looking stunned by Castiel’s attire. Which is such bullshit? Castiel is pretty sure hotel guys see nipples all the time. Ash down at the plaza has a chart. Castiel’s have gotten a perky rating. The man clears his throat. “Uh, where would you like it?”

Castiel smiles over at Dean, “Where would we like it?”

Dean stands up, straightening his clothes. “Uh, over by the bar.”

Castiel lets the man go past him, glaring at him behind his back. For some reason, Dean looks like he’s enjoying Castiel get pissed off. He’s had clients that have gotten angry for Castiel being mouthy. For being anything other than seen and not heard. Dean isn’t like that. If anything, he encourages Castiel to be a dick, just so Castiel can see him smile. Somewhere across town, Meg will be cursing his name. Castiel knows it.

The waiter puts his tray down and steps back. His hands behind his back in a mockery of a military stance. Castiel’s stomach churns at the sight. “It'll be on your bill, Mr Smith.”

“Thank you,” Dean says, walking over to examine the tray. The guy looks at Castiel expectantly. Castiel raises an eyebrow. The guy stares harder.

Dean chuckles and pulls out his wallet again. “Ah, yes. Here you go. Thank you very much.” He says handing the guy a twenty.

“Thank you very much, sir. Have a nice night.” The man says shuffling out the room with one last distasteful look at Castiel.

“You didn’t ask him for change?” Castiel says, thinking about their conversation from earlier.

Dean shakes his head pulling out two champagne glasses. “My friend is his boss if I didn’t pay him well. Sam would get on my case. Even if he was being a bit of a dick to you.”

Castiel hums walking over to Dean who opens the champagne with a soft pop. He pours Castiel a glass which he takes, twirling the stem between his fingers. “So Dean, do you have anyone else in town? A wife? Or a Girlfriend? Hell, Boyfriend?”

Dean snorts, “I have both.”

Castiel blinks at that, shocked despite himself. Most of his clients are cheaters, he’s aware of that, but for a dumb reason he thought Dean would be better than that. Not worse. “Where are they? Shopping together?” He asks bitterly, finishing his glass of champagne in one go.

Dean raises an eyebrow, pouring him another glass. “Try it was a strawberry this time it brings out the flavor.”

“Thanks,” Castiel says, picking one up and looking at Dean expectantly.

Dean sighs, “My ex-wife Lisa... is now in Santa Barbara... in my ex-home...with my ex-dog and her new husband.” Dean picks the leaves of his strawberry, avoiding Castiel’s gaze. “And my ex-girlfriend, Lydia, is in San Francisco...moving out of my apartment as we speak.”

Castiel winces, taking a much smaller sip of his champagne and bites the strawberry. He doesn’t have the heart to tell Dean he still hates the stuff. Besides alcohol is alcohol. “What about your boyfriend?”

“Ah,” Dean clears his throat eating another strawberry to avoid the conversation. “That’s been a while… back in college, I think? I have no clue where Victor ended up, to be honest with you.”

“Have you slept with guys since?” Castiel asks, wondering if that might explain Dean’s nervousness. Dean’s at least a decade older than Castiel, which means college has been a while for him. Castiel likes to take his time with inexperienced guys or guys who were out of practice. But Dean’s letting his hour waste away. If he doesn’t get on with it soon, Dean might be too nervous to finish. For some bizarre reason, Castiel doesn’t want that. He wants him to enjoy tonight. Oh, Meg is going to kill him.

Dean clears his throat, “I mean a couple of times. But honestly, I had to shove myself back in closet once my business took off.”

“Oh,” Castiel wasn’t expecting that. Not with how Dean had held his waist down in the lobby. The possessiveness of that little gesture, would be hard for anyone to miss.

Dean smiles crookedly, “I wouldn’t mind if people found out. Sure it might hurt some investments, but we’d probably still be in the green.” Dean’s face falls, a hurt look taking over his face. “My business partner he disagrees.”

“Homophobic?” Castiel asks placing his hand on Dean’s arm.

Dean laughs without humor, “No the complete opposite. But he married a woman and thinks I should do the same.” There’s a story there, Castiel can feel it, but he can also see the time on Dean’s Rolex.

“Look, Dean,” Castiel says softly. “I appreciate this whole getting to know you and this whole "slow seduction scene" you've got going. But I'm a sure thing, okay?”

“I kinda figured that out for myself Cas,” Dean says a smirk lighting up his face. He’s beautiful brooding, but like this, happy and teasing, Castiel feels like a moth to a flame.

He lets his hand wander up Dean's arm. Stroking over the cotton of his shirt. “Well I'm on an hourly rate so could we should move it along?” Castiel says, somewhat impatiently. He isn’t even ashamed to admit he wants Dean’s dick. Meg warned him off feelings, but there’s nothing wrong with lusting after a client.

Dean raises an eyebrow and Castiel gets it now, why everyone in this hotel acts like Dean’s a god. “Somehow, I'm sensing that this time problem is a major issue with you. Why don't we just get through that right now?

“Great, let's get started.” He says leaning forward. Suddenly rearing to go, whatever way Dean wants him.

Dean stops him with a palm to the chest, his lip ticks upwards. “How much for the entire night?”

Castiel blinks his brain spluttering to a halt. “A whole night?” He asks breathlessly.

Dean nods, his green eyes sparkling. Castiel’s never spent the whole night with anyone before. Two hundred bucks is usually his highest rate. But for a guy like Dean, it might be small change. “You couldn't afford it.” He says just to see what Dean does.

“Try me.”

Castiel bites his lip, coming up with a price on the fly. “Eight hundred dollars.” He says. It’s his entire rent money for tonight and the next month. He figures, he can negotiate with Dean and at least get this month’s bill in the clear. Four hundred will feel like a bargain after the price he just asked for. Except Dean doesn’t bulk at it.

“Done.” He says reaching up to undo his tie. “Now we can relax.”

Castiel swallows. Jesus Christ, he’s actually going to get paid eight hundred bucks for this bullshit. “Are you sure you want me to stay for the entire night? I mean, I could just blow you and be on my way.”

Dean chuckles, his eyes locked on Cas’s mouth. “Not that, that doesn’t sound nice Cas, but to tell you the truth. I don't want to be alone tonight.”

“Why? Is it your birthday or something?”

“No,” Dean says still sitting up straight and not offering anything else.

Castiel shrugs, its none of his business why Dean’s lonely enough to take his insane price tag. He’s his hook-up, not his therapist. “Well then, I guess that means we're getting comfortable." Castiel puts down his champagne and unzips his boots. 

Dean grins, sitting at the bar and biting into another strawberry. Castiel rolls his eyes, Dean is without a doubt, hotter than hell, when he takes control of the room like that. But Castiel likes him when he blushes and stammers. No one has ever been that way around him. It makes him feel wanted in a way he never has before. He watches Dean eat and waits for the perfect moment then says, "Y'know I have been the party at a couple of birthdays. My rates for orgies are excellent."

Dean chokes on a strawberry, Castiel snorts. Watching as Dean stammers before he gets to his feet. He needs to text Meg and let her know he won’t be home tonight. “I’m going to go to the bathroom, then we can do whatever you want okay. With a whole night ahead you’ve got plenty of options.”

Dean’s pleased laugh follows Castiel as he steps into the marble bathroom. He leans against the door and sighs; he has no idea how he’s going to survive the night without getting attached to Dean. But for eight hundred dollars he’s going to try.

  
  


**Notes for the Chapter:**

> Thank you for reading. I am aware that Viv charges £300 a night in the movie, but y'know that was the 80s this is the noughties as unfortunately inflations a thing. 
> 
> I promise the next chapter will have some smut, I can't wait to write some of the tags I have listed but the plot had to happen first. 
> 
> See you next update xx

**Author's Note:**

> If you want to reach out to me, see my progress or scream at me about the feelings I gave you, you can find me on [tumblr.](https://wingsandimpalas.tumblr.com/) Thank you for reading, I love all of you! and if you enjoyed this fic then please share the rebloggable link which you can find here.
> 
> **If your wondering when the next chapter is going to be posted[ you can check out my post explaining where I’m at with writing at the moment.](https://wingsandimpalas.tumblr.com/post/644175650410971136/writing-update-260221) **


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